Milverine (drug)

Milverine
Clinical data
Other names	Fenprin, Fenpyramine, Miospasm.
Identifiers
	IUPAC name N-(3,3-diphenylpropyl)pyridin-4-amine;
CAS Number	75437-14-8;
PubChem CID	71139;
ChemSpider	64284;
CompTox Dashboard (EPA)	DTXSID50868359 ;
Chemical and physical data
Formula	C20H20N2
Molar mass	288.394 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)C(CCNC2=CC=NC=C2)C3=CC=CC=C3;
	InChI InChI=1S/C20H20N2/c1-3-7-17(8-4-1)20(18-9-5-2-6-10-18)13-16-22-19-11-14-21-15-12-19/h1-12,14-15,20H,13,16H2,(H,21,22); Key:KMZHYAUKFHLFNY-UHFFFAOYSA-N;

Milverine is a spasmolytic (antispasmodic) agent that was developed in the latter half of the 20th century.^[1]^[2]^[3]

The therapeutic use of fenpyramin as a platelet-antiaggregating and antithrombotic as well as vasodilating and antianginous medicine was also identified.^[4]

Milverine is a bifunctional molecule; 1 half of the molecule contains 3,3-Diphenylpropylamine and the other half of the molecule contains fampridine.

Synthesis

The chemical synthesis of milverine was identified.^[5]

Conjugate soft addition of benzene to cinnamic acid [140-10-3] (1) gives 3,3-diphenylpropionic acid [606-83-7] (2). Halogenation with thionyl chloride gives 3,3-diphenylpropionyl chloride [37089-77-3] (3). Schotten-Baumann reaction with 4-aminopyridine (Fampridine) [504-24-5] (4) gives 3,3-diphenyl-N-(4-pyridyl)propionamide [75437-13-7] (5). The last step involves reduction of the amide bond giving milverine (6), respectively.

References

^ Carpenedo F, Santi-soncin E. [Spasmolytic activity of a new diphenylpropylaminic derivative, N-(4'-pyridyl)-3,3-diphenyl 1-aminopropane]. Minerva Med. 1970;61(43):2417-24. PMID: 5425728.
^ Baldi, F. et al, Curr. Ther. Res., 1984,36, 267 (pharmacol)
^ Fossati A, Sosio A, Pellegrini R, Frigo GM, D'Angelo L, Lecchini S, Marcoli M, Caravaggi M, Crema A. Milverine: in vitro and in vivo activity on the animal and human colon. Farmaco Prat. 1986 Sep;41(9):279-89. PMID: 3770157.
^ Rinaldo Pellegrini, Gaetano Clavenna, Piero Bellani, EP0143082 (1985 to RBS PHARMA (ROGER BELLON SCHOUM) S.p.A.).
^ Paolo Masi, Angela Monopoli, Adone Carlo Saravalle, Cesare Zio, DE3002909 (1980 to Italiana Schoum Spa).

[1] Carpenedo F, Santi-soncin E. [Spasmolytic activity of a new diphenylpropylaminic derivative, N-(4'-pyridyl)-3,3-diphenyl 1-aminopropane]. Minerva Med. 1970;61(43):2417-24. PMID: 5425728.

[2] Baldi, F. et al, Curr. Ther. Res., 1984,36, 267 (pharmacol)

[3] Fossati A, Sosio A, Pellegrini R, Frigo GM, D'Angelo L, Lecchini S, Marcoli M, Caravaggi M, Crema A. Milverine: in vitro and in vivo activity on the animal and human colon. Farmaco Prat. 1986 Sep;41(9):279-89. PMID: 3770157.

[4] Rinaldo Pellegrini, Gaetano Clavenna, Piero Bellani, EP0143082 (1985 to RBS PHARMA (ROGER BELLON SCHOUM) S.p.A.).

[5] Paolo Masi, Angela Monopoli, Adone Carlo Saravalle, Cesare Zio, DE3002909 (1980 to Italiana Schoum Spa).

[1]

[2]

[3]

[4]

[5]

v t e Urologicals, including antispasmodics (G04B)
Acidifiers	Ammonium chloride Calcium chloride
Urinary antispasmodics (primarily antimuscarinics)	Darifenacin Desfesoterodine Emepronium Fesoterodine Flavoxate Imidafenacin Meladrazine Mirabegron Oxybutynin Propiverine Solifenacin Terodiline Tolterodine Trospium chloride Vibegron
Other urologicals	Urea analogues: Acetohydroxamic acid Salicylhydroxamic acid Other: Collagen Dapoxetine Dimethyl sulfoxide Magnesium hydroxide Pentosan polysulfate Phenazopyridine Phenyl salicylate Succinimide Tiopronin

v t e Irritable bowel syndrome (IBS)
Management	Low-FODMAP diet Gluten-free diet Soluble fiber Laxatives Antispasmodics Psychotherapy Tricyclic antidepressants SSRIs Probiotics Eluxadoline
Related topics	Gut–brain axis Hypothalamic–pituitary–adrenal axis Sympathetic nervous system